Sodium Thiosulfate → 3-Allyloxy-pyridine-2-carbaldehyde

HRID 1592380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592380
[CH2:1]([O:4][C:5]1[C:6]([CH2:11][OH:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:4][C:5]1[C:6]([CH:11]=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 14598977(3-Allyloxy-pyridin-2-yl)-methanol

Produkt 1

HCID 450909933-Allyloxy-pyridine-2-carbaldehydeAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (3-allyloxy-pyridin-2-yl)-methanol (2.08 g, 12.6 mmol) (Chen, Y. L. Eur. Pat. Appl. (1985), EP 150984) in CH2Cl2 (60 mL) was added Dess-Martin Periodinane (5.82 g, 13.7 mmol), and stirred at room temperature for 24 hours. CH2Cl2 (40 mL), saturated NaHCO3 (30 mL), and aqueous sodium thiosulfate (30 mL) were added and stirred for 40 minutes. The layers were separated and the aqueous phase was extracted with CH2Cl2 (2×50 mL). The combined organic extracts were washed with brine (1×75 mL), dried (Na2SO4), and concentrated to provide 2.02 g (98%) of 3-allyloxy-pyridine-2-carbaldehyde as a brown oil. 1H NMR (CDCl3) δ 4.71 (d, 2H, J=6.0 Hz), 5.37 (d, 1H, J=12.0 Hz), 5.50 (d, 1H, J=18.0 Hz), 5.99-6.12 (m, 1H), 7.38-7.48 (m, 2H), 8.40 (d, 1H, J=3.0 Hz), 10.41 (s, 1H).

Aufarbeitung

  1. stirringstirred for 40 minutes
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (2×50 mL)
  4. washThe combined organic extracts were washed with brine (1×75 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c1cfeef8b5b84c0bbdb6482a138618d2
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291631B2

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